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Holiday Homes in Oakland

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Featured Holiday Homes in Oakland

Sister A-Frame in Woods B

10.0 out of 10, Exceptional, (6)
"Great stay. Would stay here again if in the area."
The price is AU$355
includes taxes & fees
9 Oct - 10 Oct
Sister A-Frame in Woods B

Discover Oakland charm near Colby College 10 min

2.0 star property
10.0 out of 10, Exceptional, (4)
"New, clean and had everything we needed. "
The price is AU$415
includes taxes & fees
15 Oct - 16 Oct
Discover Oakland charm near Colby College 10 min

Charming 1840s farmhouse with donkeys, wood stove, fire pit, and full kitchen

10.0 out of 10, Exceptional, (7)
"Six of us stayed to celebrate my son’s graduation from Thomas College. It was perfect! The property has a beautiful Balance of rustic farmhouse and modern conveniences. Our host was wonderful, the check in was easy, the house was immaculate, and the beds were comfy. I would stay here again! "
The price is AU$476
includes taxes & fees
5 Oct - 6 Oct
Charming 1840s farmhouse with donkeys, wood stove, fire pit, and full kitchen

Cozy Cottage on water's edge of Lake Cobbosseecontee

8.8 out of 10, Excellent, (15)
"Perfect old fashion Maine cottage! Great sunsets!"
The price is AU$484
includes taxes & fees
15 Oct - 16 Oct
Cozy Cottage on water's edge of Lake Cobbosseecontee

Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine

10.0 out of 10, Exceptional, (2)
"The property was very clean & in a quiet area. Very comfortable & inviting."
The price is AU$232
includes taxes & fees
5 Oct - 6 Oct
Charming 1-bedroom building with WiFi, AC in brilliant Madison Maine

The Maine Experience: Where expansive nature meets modern comfort...

10.0 out of 10, Exceptional, (1)
"A great spot for all 7 of us. Nice house with zones for everyone. Lovely backyard. Big kitchen and dining table"
The price is AU$564
includes taxes & fees
14 Oct - 15 Oct
The Maine Experience: Where expansive nature meets modern comfort...

Zeus's Landing at Cottages of Maine Gradual beachfront, King Beds, Dog Friendly

10.0 out of 10, Exceptional, (3)
"Great spot on the lake! The house was super clean, beds were very comfortable, kitchen was well stocked and had everything we needed while we were there. The neighbor's house is really close to the property along the shared beach, and while it was never an issue for us, you may hear the neighbors as they come and go from their house. Overall a fantastic stay."
The price is AU$601
includes taxes & fees
6 Oct - 7 Oct
Zeus's Landing at Cottages of Maine Gradual beachfront, King Beds, Dog Friendly

Lakefront, Stunning Home only 30 min to Sugarloaf!

10.0 out of 10, Exceptional, (36)
"The house was very comfortable. Grass and lake well maintained. Plenty of towels and the whirlpool bath was very a nice bonus. Kayaks were fun. "
The price is AU$784
includes taxes & fees
4 Oct - 5 Oct
Lakefront, Stunning Home only 30 min to Sugarloaf!

Charming Lakefront Home: Big Porches, Kayaks & Room to Gather

9.6 out of 10, Exceptional, (4)
"Wonderful stay! This is the third year in a row our group of "mature" fishermen have stayed at this lake. This was by far the best place we stayed at. Views and setting are all that we could ask for. We'll be back again."
The price is AU$1,095
includes taxes & fees
19 Oct - 20 Oct
Charming Lakefront Home: Big Porches, Kayaks & Room to Gather

A soul soothing escape. Artistically built and lovingly maintained.

10.0 out of 10, Exceptional, (29)
"We loved the property. The Views are great and it is very comfortable and quiet. I would highly recommend staying here."
The price is AU$634
includes taxes & fees
6 Oct - 7 Oct
A soul soothing escape. Artistically built and lovingly maintained.

Minimal & Cozy Victorian Private Room in Downtown Skowhegan

The price is AU$615
includes taxes & fees
12 Oct - 13 Oct
Minimal & Cozy Victorian Private Room in Downtown Skowhegan
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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